ethyl 4,4-difluoro-3-hydroxybutanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled solution of ethyl 4,4-difluoro-3-oxobutanoate (5.0 g, 30.1 mmol) in toluene (150 mL) was added NaBH4 (1.26 g, 33.1 mmol) at 0° C. The mixture was then stirred at RT for 4.5 hours. The reaction was quenched with aqueous HCl (10%) carefully. The separated aqueous phase was extracted with EtOAc (20 mL×2). The combined organic phases were dried over Na2SO4, and then filtered and then concentrated in vacuo to give the crude ethyl 4,4-difluoro-3-hydroxybutanoate as colorless oil (3.8 g, yield: 76%). The reaction was quenched with aqueous HCl (10%) carefully The separated aqueous phase was extracted with EtOAc (20 mL×2) The combined organic phases were dried over Na2SO4 filtered concentrated in vacuo